EP0645374B1 - Compose 5-amino-2-phenoxylsulfonanilide - Google Patents

Compose 5-amino-2-phenoxylsulfonanilide Download PDF

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Publication number
EP0645374B1
EP0645374B1 EP93909405A EP93909405A EP0645374B1 EP 0645374 B1 EP0645374 B1 EP 0645374B1 EP 93909405 A EP93909405 A EP 93909405A EP 93909405 A EP93909405 A EP 93909405A EP 0645374 B1 EP0645374 B1 EP 0645374B1
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EP
European Patent Office
Prior art keywords
compound
sodium
amino
reaction
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP93909405A
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German (de)
English (en)
Other versions
EP0645374A4 (fr
EP0645374A1 (fr
Inventor
Kensei Taisho Pharmaceutical Co. Ltd. Yoshikawa
Shuji Taisho Pharmaceutical Co. Ltd. Saito
Yohichi Taisho Pharmaceutical Co. Ltd. Shimazaki
Mariko Taisho Pharmaceutical Co. Ltd. Kashiwa
Katsuo Taisho Pharmaceutical Co. Ltd. Hatayama
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Taisho Pharmaceutical Co Ltd
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Taisho Pharmaceutical Co Ltd
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Application filed by Taisho Pharmaceutical Co Ltd filed Critical Taisho Pharmaceutical Co Ltd
Publication of EP0645374A4 publication Critical patent/EP0645374A4/fr
Publication of EP0645374A1 publication Critical patent/EP0645374A1/fr
Application granted granted Critical
Publication of EP0645374B1 publication Critical patent/EP0645374B1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Definitions

  • the present invention relates to a 5-amino-2-phenoxysulfonanilide compound having anti-inflammatory, antipyretic, analgesic and antirheumatic actions.
  • An object of the present invention is to provide drugs having excellent anti-inflammatory, antipyretic, analgesic and antirheumatic actions.
  • the present invention relates to a 5-amino-2-phenoxysulfonanilide compound represented by Formula (I): and to pharmaceutically acceptable salts thereof.
  • the salt refers to salts with alkali metals (e.g. sodium and potassium), alkaline earth metals (e.g. calcium and magnesium), ammonia and organic bases (e.g. ethanolamine, lysine and arginine).
  • alkali metals e.g. sodium and potassium
  • alkaline earth metals e.g. calcium and magnesium
  • ammonia and organic bases e.g. ethanolamine, lysine and arginine.
  • the compound of Formula (I) of the present invention can be prepared, for example, by the following preparation steps (a) to (f).
  • the hydrolysis in this reaction may be a conventional hydrolysis of an amide under the basic or acidic condition, for example, a hydrolysis using lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide or potassium t-butoxide for the basic condition, or a hydrolysis using hydrochloric acid, hydrobromic acid or sulfuric acid for the acidic condition.
  • Examples of the solvent to be used in the reaction are water, methanol, ethanol, propanol, t-butanol, tetrahydrofuran, dioxane, benzene, toluene, xylene, chlorobenzene, N,N-dimethylformamide, dimethyl sulfoxide, formic acid and acetic acid, but it is preferably that the solvent is appropriately chosen depending on the condition of the hydrolysis.
  • the compound of the present invention can be administered orally or parenterally in the conventional dosage forms such as, for example, tablets, dusts, granules, powders, capsules, solutions, emulsions, suspensions and injections, all of which can be prepared by conventional practices.
  • the dose used for humans as an anti-inflammatory, antipyretic, analgesic or antirheumatic agent is different depending on the age and body weight of the patient, symptoms of the disease, route of administration and frequency of administration, but it is usually from 5 to 600 mg per day.
  • the compound which is an active ingredient in the present invention has potent anti-inflammatory, antipyretic, analgesic and antirheumatic actions with fewer side effects such as gastrointestinal disorders, and therefore it is useful as anti-inflammatory, antipyretic, analgesic or antirheumatic agents.
  • test drugs the compound (a) of the present invention and the control drug (b)
  • test drugs each suspended in 5% aqueous gum arabic solution in an amount of 1 ml per 100 g of body weight.
  • 0.1 ml of 1% carrageenin was administered subcutaneously into the left hind foot pad.
  • the volume of the foot was determined, and the edema inhibition rate (%) was calculated for the anti-inflammatory effect.
  • Dose of the test drug was 0.3 mg/kg.
  • mice Seven Lewis strain rats (for each group) were administered subcutaneously 0.7% Mycobacterium tuberculosis suspended in liquid paraffin into the left hind foot pad to induce adjuvant arthritis. 15 ⁇ 18 Days after administration of adjuvant, rats with fully developed arthritis were administered orally with test drugs [the compound (a) of the present invention and the control compound (b)], each suspended in 5% aqueous gum arabic solution in an amount of 1 ml per 100 g of body weight once a day for 4 days.
  • test drugs the compound (a) of the present invention and the control compound (b)
  • the volume of the foot was determined, and the edema inhibition rate (%) was calculated for the therapeutical effect.
  • Dose of the test drug was 0.2 mg/kg.
  • test drugs the compound (a) of the present invention and the control compound (b)
  • test drugs each suspended in 5% aqueous gum arabic solution in an amount of 1 ml per 100 g of body weight.
  • the occurrence of squeaking response was monitored with time over 5 hours after the administration, and the inhibition rate (%) was calculated to examine the analgesic effect.
  • Dose of the test drug was 1.0 mg/kg.
  • the compound (a) of the present invention the compound of Example 1.
  • Control compound (b) N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
  • Healthy human peripheral blood heparinized was layered over Lymphoprep (Daiichi Pharmaceutical Co.) under aseptic conditions to remove red blood cell, and the cell counts were adjusted to 2 ⁇ 10 6 cells/ml by froating the cells in RPMI-1640 medium containing 10% fatal bovine serum, penicillin 100U/ml, streptomycin 100U/ml, HEPES buffer 10mM and L-glutamin 2mM.
  • the concentrations of the test drug were 0, 3, 10 and 30 ⁇ g/ml.
  • IC 50 value of the 1L-1 formation inhibiting action of the compound (a) of the present invention was 13.3 ⁇ g/ml, but the control compound (b) did not show 50% or more inhibition in the above concentration, and therefore the IC 50 value could not be calculated.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Claims (2)

  1. Composé représenté par la formule:
    Figure imgb0016
     ou un sel de celui-ci.
  2. Procédé pour la préparation d'un composé représenté par la formule (b):
    Figure imgb0017
     ou d'un sel de celui-ci, qui comprend le fait d'hydrolyser un composé de Formule (a):
    Figure imgb0018
     dans laquelle R est un groupe alkyle ayant 1 à 5 atomes de carbone, un groupe alcoxy ayant 1 à 5 atomes de carbone ou un groupe alcoxycarbonyle ayant 2 à 6 atomes de carbone et éventuellement le fait de transformer le composé de Formule (b) en un sel de celui-ci.
EP93909405A 1992-06-12 1993-04-21 Compose 5-amino-2-phenoxylsulfonanilide Expired - Lifetime EP0645374B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP152554/92 1992-06-12
JP15255492 1992-06-12
PCT/JP1993/000518 WO1993025520A1 (fr) 1992-06-12 1993-04-21 Compose 5-amino-2-phenoxylsulfonanilide

Publications (3)

Publication Number Publication Date
EP0645374A4 EP0645374A4 (fr) 1995-02-14
EP0645374A1 EP0645374A1 (fr) 1995-03-29
EP0645374B1 true EP0645374B1 (fr) 1996-11-20

Family

ID=15543009

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93909405A Expired - Lifetime EP0645374B1 (fr) 1992-06-12 1993-04-21 Compose 5-amino-2-phenoxylsulfonanilide

Country Status (11)

Country Link
US (1) US5449826A (fr)
EP (1) EP0645374B1 (fr)
KR (1) KR0150826B1 (fr)
AT (1) ATE145395T1 (fr)
AU (1) AU661906B2 (fr)
CA (1) CA2137780C (fr)
DE (1) DE69306113T2 (fr)
DK (1) DK0645374T3 (fr)
ES (1) ES2097505T3 (fr)
GR (1) GR3021821T3 (fr)
WO (1) WO1993025520A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019318A1 (fr) * 1993-02-19 1994-09-01 Taisho Pharmaceutical Co., Ltd. Compose de 5-aminoacetylaminosulfonanilide
DE19533644A1 (de) * 1995-09-12 1997-03-13 Nycomed Arzneimittel Gmbh Neue Benzolsulfonamide
DE19533643A1 (de) * 1995-09-12 1997-03-13 Nycomed Arzneimittel Gmbh Neue cyclische Derivate von Benzolsulfonamiden

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531552A (en) * 1967-05-04 1970-09-29 Eaton Yale & Towne Method of making composite load supporting structure
US3840597A (en) * 1971-02-24 1974-10-08 Riker Laboratories Inc Substituted 2-phenoxy alkane-sulfonanilides
US3856859A (en) * 1973-06-08 1974-12-24 Riker Laboratories Inc Selective nitration process
GB8631083D0 (en) * 1986-12-31 1987-02-04 Fujisawa Pharmaceutical Co 2'-phenoxyalkanesulfonanilide derivatives
PT86407B (pt) * 1986-12-31 1990-11-20 Fujisawa Pharmaceutical Co Processo para a preparacao de novos derivados de alcano-sulfonanilida, e de composicoes farmaceuticas compreendendo os mesmos
JPH0611747B2 (ja) * 1987-11-19 1994-02-16 大正製薬株式会社 スルホンアニリド化合物
US4885367A (en) * 1987-11-19 1989-12-05 Taisho Pharmaceutical Co., Ltd. Sulfonanilide compounds
JPH0222260A (ja) * 1988-07-11 1990-01-25 Taisho Pharmaceut Co Ltd 置換スルホンアニリド
JPH02300122A (ja) * 1989-05-12 1990-12-12 Taisho Pharmaceut Co Ltd 消炎・鎮痛・解熱剤
US5374764A (en) * 1991-08-08 1994-12-20 Taisho Pharmaceutical Co., Ltd. 5-aminosulfonanilide compounds
WO1994019318A1 (fr) * 1993-02-19 1994-09-01 Taisho Pharmaceutical Co., Ltd. Compose de 5-aminoacetylaminosulfonanilide

Also Published As

Publication number Publication date
DE69306113T2 (de) 1997-03-13
ES2097505T3 (es) 1997-04-01
AU4022493A (en) 1994-01-04
ATE145395T1 (de) 1996-12-15
DE69306113D1 (de) 1997-01-02
US5449826A (en) 1995-09-12
EP0645374A4 (fr) 1995-02-14
KR0150826B1 (ko) 1998-10-15
WO1993025520A1 (fr) 1993-12-23
CA2137780C (fr) 1998-06-09
AU661906B2 (en) 1995-08-10
KR950701617A (ko) 1995-04-28
CA2137780A1 (fr) 1993-12-23
EP0645374A1 (fr) 1995-03-29
GR3021821T3 (en) 1997-02-28
DK0645374T3 (da) 1996-12-23

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